Peter Schiff Warns Michael Saylor Will Sell Bitcoin at Lower Prices Again

Peter Schiff and Michael Saylor are in another heated X argument after the infamous gold bug Schiff warned investors about more future Bitcoin sales in the future.

Peter Schiff argued that Michael Saylor sold over 4k Bitcoin near the local bear market bottom of $62,000 then bought back those same Bitcoin over $80,000. He posted a lengthy attack on X and criticized Saylor for poorly timing the crypto markets:

During its last Bitcoin selling spree, Strategy sold 6,948 Bitcoin for approximately $431.8 million in net proceeds, or about $62,150 per Bitcoin. Now he's buying back some of what he sold for over $80K per Bitcoin. It won't be long before he's selling at lower prices again.

— Peter Schiff (@PeterSchiff) September 22, 2026

Why Did Michael Saylor Sell 6,948 Bitcoin near the Q3 Bitcoin Bottom?

Michael Saylor sold Bitcoin to fund the company’s USD and cash reserves to fund Strategy’s Stretch (NASDAQ: STRC) dividend payments. As of Q3 2026, Strategy pays around $1.6 billion annually in preferred dividend to shareholders.

The problem is that STRC hasn’t traded above $100 since May 2026 so there haven’t been any new accretive STRC funded Bitcoin buys since then.

Schiff does have an interesting point! Saylor may have to continue panic selling Bitcoin in order to keep the USD reserve large enough to support dividend payments. Currently, the USD cash reserve covers around 3.6 years of preferred stock dividends.

It’s interesting to see both Schiff and Saylor go back and forth but we won’t know the truth about Strategy’s massive dividend obligations until Bitcoin either goes up or down over the next several months.